Cesium carbonate → Ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

HRID 1844186ノート

反応式

HRID 1844186 の反応式
Cl.Cl[CH2:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][N:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:17][C:18]1[C:19]2[N:20]([C:25]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:26]([CH3:28])[N:27]=2)[CH:21]=[C:22]([CH3:24])[CH:23]=1>CN(C=O)C>[F:10][C:9]1[C:4]([CH2:3][O:17][C:18]2[C:19]3[N:20]([C:25]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:26]([CH3:28])[N:27]=3)[CH:21]=[C:22]([CH3:24])[CH:23]=2)=[N:5][CH:6]=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 197038622-(Chloromethyl)-3-fluoropyridine HydrochlorideHCID 86717883Ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

生成物 1

HCID 86718213Ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

15.78 g (86.7 mmol) of 2-(chloromethyl)-3-fluoropyridine hydrochloride (commercially available; additionally described in: U.S. Pat. No. 5,593,993 A1, 1997; WO2007/2181 A2, 2007) and 94.06 g (288.9 mmol) of caesium carbonate were added to 16.92 g (72.2 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate from Example 87A in 956 ml of DMF. The reaction mixture was stirred at 60° C. overnight. The reaction mixture was cooled to RT and filtered, the filtercake was washed with ethyl acetate and the filtrate was concentrated. About 500 ml of water were added to the residue and the precipitated solid was filtered off and dried under high vacuum. This gave 24.1 g (93% of theory) of the target compound.

後処理

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. washthe filtercake was washed with ethyl acetate
  4. concentrationthe filtrate was concentrated
  5. additionAbout 500 ml of water were added to the residue
  6. filtrationthe precipitated solid was filtered off
  7. customdried under high vacuum

出典と根拠

ORDレコード
ord-36e3aa79bf064e73a81448d376572306
出典データセット
uspto-grants-2015_02
特許番号
US08946215B2

反応ノート

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